JP4291880B2 - アルミノキサン類の製造方法 - Google Patents
アルミノキサン類の製造方法 Download PDFInfo
- Publication number
- JP4291880B2 JP4291880B2 JP53808997A JP53808997A JP4291880B2 JP 4291880 B2 JP4291880 B2 JP 4291880B2 JP 53808997 A JP53808997 A JP 53808997A JP 53808997 A JP53808997 A JP 53808997A JP 4291880 B2 JP4291880 B2 JP 4291880B2
- Authority
- JP
- Japan
- Prior art keywords
- aluminum
- trimethylaluminum
- solution
- water
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 191
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical group C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims description 114
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 113
- 229910052782 aluminium Inorganic materials 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 58
- CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical group C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 54
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 52
- 239000002904 solvent Substances 0.000 claims description 50
- -1 hydrocarbyl aluminum Chemical compound 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 34
- 239000007788 liquid Substances 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 23
- 239000012442 inert solvent Substances 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 16
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- 150000002430 hydrocarbons Chemical class 0.000 claims description 15
- 238000004821 distillation Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 9
- 238000001704 evaporation Methods 0.000 claims description 8
- 230000008020 evaporation Effects 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 238000011084 recovery Methods 0.000 claims description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 239000012528 membrane Substances 0.000 claims description 4
- 230000003134 recirculating effect Effects 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims 1
- 239000006193 liquid solution Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 55
- 239000000047 product Substances 0.000 description 23
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 125000005234 alkyl aluminium group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 2
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 2
- WCFQIFDACWBNJT-UHFFFAOYSA-N $l^{1}-alumanyloxy(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]O[Al] WCFQIFDACWBNJT-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000011021 bench scale process Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- LWBWGOJHWAARSS-UHFFFAOYSA-N diethylalumanyloxy(diethyl)alumane Chemical compound CC[Al](CC)O[Al](CC)CC LWBWGOJHWAARSS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- CNWZYDSEVLFSMS-UHFFFAOYSA-N tripropylalumane Chemical compound CCC[Al](CCC)CCC CNWZYDSEVLFSMS-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
- C07F5/068—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage) preparation of alum(in)oxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/635,358 | 1996-04-19 | ||
US08/635,358 US5606087A (en) | 1996-04-19 | 1996-04-19 | Process for making aluminoxanes |
US08/680,087 | 1996-07-15 | ||
US08/680,087 US5663394A (en) | 1996-07-15 | 1996-07-15 | High yield aluminoxane synthesis process |
PCT/US1997/005554 WO1997040053A1 (en) | 1996-04-19 | 1997-04-02 | Process for making aluminoxanes |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008284860A Division JP5066058B2 (ja) | 1996-04-19 | 2008-11-05 | アルミノキサン類の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2000509040A JP2000509040A (ja) | 2000-07-18 |
JP4291880B2 true JP4291880B2 (ja) | 2009-07-08 |
Family
ID=27092356
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53808997A Expired - Fee Related JP4291880B2 (ja) | 1996-04-19 | 1997-04-02 | アルミノキサン類の製造方法 |
JP2008284860A Expired - Fee Related JP5066058B2 (ja) | 1996-04-19 | 2008-11-05 | アルミノキサン類の製造方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008284860A Expired - Fee Related JP5066058B2 (ja) | 1996-04-19 | 2008-11-05 | アルミノキサン類の製造方法 |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0906319B2 (es) |
JP (2) | JP4291880B2 (es) |
CA (1) | CA2252365A1 (es) |
DE (1) | DE69705722T3 (es) |
ES (1) | ES2160941T5 (es) |
WO (1) | WO1997040053A1 (es) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8668389B2 (en) | 2000-11-07 | 2014-03-11 | Davis-Standard, Llc | Combination thrust flange and thrust plate |
JP5440788B2 (ja) * | 2010-03-11 | 2014-03-12 | 東ソー・ファインケム株式会社 | フロー型反応器を用いたアルミノキサン組成物の製造方法 |
JP6108704B2 (ja) | 2011-07-13 | 2017-04-05 | ダウ グローバル テクノロジーズ エルエルシー | 有機金属化合物精製 |
JP6054659B2 (ja) | 2011-07-13 | 2016-12-27 | ダウ グローバル テクノロジーズ エルエルシー | 有機金属化合物精製および装置 |
EP2559681B1 (en) | 2011-08-15 | 2016-06-22 | Dow Global Technologies LLC | Organometallic compound preparation |
EP2559682B1 (en) | 2011-08-15 | 2016-08-03 | Rohm and Haas Electronic Materials LLC | Organometallic compound preparation |
SG10201801424YA (en) | 2013-02-08 | 2018-04-27 | Mitsui Chemicals Inc | Solid polyaluminoxane composition, olefin polymerization catalyst, olefin polymer production method and solid polyaluminoxane composition production method |
RU2720010C1 (ru) | 2016-11-09 | 2020-04-23 | Бриджстоун Корпорейшн | Блок-сополимеры полибутадиена и полиизопрена с высоким содержанием цис-1,4-связей |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2363888A1 (de) † | 1973-12-21 | 1975-07-03 | Auer Hans Heinrich | Vorrichtung mit rotierenden werkzeugen zur kontinuierlichen behandlung von stoffen in fliessfaehiger form |
US4730072A (en) * | 1986-08-15 | 1988-03-08 | Shell Oil Company | Process for preparing aluminoxanes |
US4908463A (en) * | 1988-12-05 | 1990-03-13 | Ethyl Corporation | Aluminoxane process |
US4924018A (en) † | 1989-06-26 | 1990-05-08 | Ethyl Corporation | Alkylaluminoxane process |
DE4004477A1 (de) † | 1990-02-14 | 1991-08-22 | Schering Ag | Verfahren zur herstellung von loesungen oligomerer methylaluminoxane |
US5041585A (en) * | 1990-06-08 | 1991-08-20 | Texas Alkyls, Inc. | Preparation of aluminoxanes |
US5248801A (en) * | 1992-08-27 | 1993-09-28 | Ethyl Corporation | Preparation of methylaluminoxanes |
DE4314986A1 (de) * | 1993-05-06 | 1994-11-10 | Witco Gmbh | Verfahren zur Herstellung von Aluminoxanen |
US5599964A (en) * | 1996-04-19 | 1997-02-04 | Albemarle Corporation | Continuous process for preparing hydrocarbylaluminoxanes |
DE10133728A1 (de) * | 2001-07-11 | 2003-01-23 | Bayer Ag | Verfahren zur Herstellung von (cyclo)aliphatischen Diisocyanaten |
-
1997
- 1997-04-02 EP EP97917847A patent/EP0906319B2/en not_active Expired - Lifetime
- 1997-04-02 CA CA 2252365 patent/CA2252365A1/en not_active Abandoned
- 1997-04-02 DE DE69705722T patent/DE69705722T3/de not_active Expired - Lifetime
- 1997-04-02 JP JP53808997A patent/JP4291880B2/ja not_active Expired - Fee Related
- 1997-04-02 WO PCT/US1997/005554 patent/WO1997040053A1/en active IP Right Grant
- 1997-04-02 ES ES97917847T patent/ES2160941T5/es not_active Expired - Lifetime
-
2008
- 2008-11-05 JP JP2008284860A patent/JP5066058B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ES2160941T5 (es) | 2007-06-01 |
WO1997040053A1 (en) | 1997-10-30 |
DE69705722T2 (de) | 2002-05-08 |
EP0906319A1 (en) | 1999-04-07 |
EP0906319B2 (en) | 2006-12-06 |
DE69705722T3 (de) | 2007-04-26 |
JP2009073849A (ja) | 2009-04-09 |
JP2000509040A (ja) | 2000-07-18 |
ES2160941T3 (es) | 2001-11-16 |
EP0906319B1 (en) | 2001-07-18 |
DE69705722D1 (de) | 2001-08-23 |
CA2252365A1 (en) | 1997-10-30 |
JP5066058B2 (ja) | 2012-11-07 |
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